SCOPUS 정보 검색 플랫폼

Volumn , Issue 11, 2008, Pages 1703-1705

Synthesis of pharmacologically active apomorphines by direct N-substitution on the aporphine backbone

Author keywords

Alkaloids; Medicinal chemistry; Oxidations; Protecting groups; Transition metals

Indexed keywords

APOCODEINE; APOMORPHINE; APOMORPHINE DERIVATIVE; APORPHINE DERIVATIVE;

ALKYLATION; ARTICLE; DEMETHYLATION; DEPROTECTION REACTION; DRUG SYNTHESIS; OXIDATION; SUBSTITUTION REACTION;

EID: 48249135153 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078494 Document Type: Article

Times cited : (7)

References (29)

1
- 2642522343
- Cordell, G. A, Ed, Academic: New York
- Ríos, J. L.; Máñez, S.; Giner, R. M.; Recio, M. C. The Alkaloids, Vol. 53; Cordell, G. A., Ed.; Academic: New York, 2000, 57.
- (2000) The Alkaloids , vol.53 , pp. 57
- Ríos, J.L.¹ Máñez, S.² Giner, R.M.³ Recio, M.C.⁴

2
- 3543059896
- For recent reviews, see: a
- For recent reviews, see: (a) Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 3341.
- (2004) Chem. Rev , vol.104 , pp. 3341
- Chrzanowska, M.¹ Rozwadowska, M.D.²

3
- 33947408185
- (b) Griesbeck, A. G.; Hoffmann, N.; Warzecha, K. D. Acc. Chem. Res. 2007, 40, 128.
- (2007) Acc. Chem. Res , vol.40 , pp. 128
- Griesbeck, A.G.¹ Hoffmann, N.² Warzecha, K.D.³

4
- 34249799653
- (c) Lefrance, M.; Blaquiere, N.; Fagnou, K. Eur. J. Org. Chem. 2007, 811.
- (2007) Eur. J. Org. Chem , pp. 811
- Lefrance, M.¹ Blaquiere, N.² Fagnou, K.³

5
- 0004116741
- Plenum Press: New York London
- Casy, A. F.; Parfitt, R. T. Opioid Analgesics; Plenum Press: New York London, 1986.
- (1986) Opioid Analgesics
- Casy, A.F.¹ Parfitt, R.T.²

6
- 0027958964
- (a) Guinaudeau, H.; Leboeuf, M.; Cavé, A. J. Nat. Prod. 1994, 57, 1033.
- (1994) J. Nat. Prod , vol.57 , pp. 1033
- Guinaudeau, H.¹ Leboeuf, M.² Cavé, A.³

7
- 17844365006
- and references therein
- (b) Clement, J. A.; Yode, B. J.; Kingston, D. G. I. Mini-Rev. Org. Chem. 2004, 1, 183; and references therein.
- (2004) Mini-Rev. Org. Chem , vol.1 , pp. 183
- Clement, J.A.¹ Yode, B.J.² Kingston, D.G.I.³

8
- 33846441262
- (a) Zhang, A.; Zhang, Y.; Branfman, A. R.; Baldessarini, R. J.; Neumeyer, J. L. J. Med. Chem. 2007, 50, 171.
- (2007) J. Med. Chem , vol.50 , pp. 171
- Zhang, A.¹ Zhang, Y.² Branfman, A.R.³ Baldessarini, R.J.⁴ Neumeyer, J.L.⁵

9
- 33846905526
- and references therein
- (b) Zhang, A.; Neumeyer, J. L.; Baldessarini, R. J. Chem. Rev. 2007, 107, 274; and references therein.
- (2007) Chem. Rev , vol.107 , pp. 274
- Zhang, A.¹ Neumeyer, J.L.² Baldessarini, R.J.³

10
- 48249155291
- DOI: 10.2174/156801405774330421
- Berényi, S.; Csutorás, Cs.; Sipos, A. Curr. Med. Chem. 2008, DOI: 10.2174/156801405774330421.
- (2008) Curr. Med. Chem
- Berényi, S.¹ Csutorás, C.² Sipos, A.³

11
- 66449085731
- (a) Speyer, E.; Rosenfeld, H. Ber. Dtsch. Chem. Ges. 1925, 58, 1125.
- (1925) Ber. Dtsch. Chem. Ges , vol.58 , pp. 1125
- Speyer, E.¹ Rosenfeld, H.²

12
- 0014186871
- (b) Bertgen, C.; Fleischhacker, W.; Vielböck, F. Chem. Ber. 1967, 100, 3002.
- (1967) Chem. Ber , vol.100 , pp. 3002
- Bertgen, C.¹ Fleischhacker, W.² Vielböck, F.³

13
- 0019133927
- (c) Hosztafi, S.; Makleit, S.; Bognár, R. Acta Chim. Acad. Sci. Hung. 1980, 103, 371.
- (1980) Acta Chim. Acad. Sci. Hung , vol.103 , pp. 371
- Hosztafi, S.¹ Makleit, S.² Bognár, R.³

14
- 33749274014
- Hosztafi, S.; Makleit, S. ACH-Models Chem. 1996, 133, 401.
- (1996) ACH-Models Chem , vol.133 , pp. 401
- Hosztafi, S.¹ Makleit, S.²

15
- 27144453646
- Søndergaard, K.; Kristensen, J. L.; Gillings, N.; Begtrup, M. Eur. J. Org.Chem. 2005, 4428.
- (2005) Eur. J. Org.Chem , pp. 4428
- Søndergaard, K.¹ Kristensen, J.L.² Gillings, N.³ Begtrup, M.⁴

16
- 0036026290
- Garrido, J. M. P. J.; Delerue-Matos, C.; Borges, F.; Macedo, T. R. A.; Oliveira-Brett, A. M. J. Chem. Soc., Perkin Trans. 2 2002, 1713.
- (2002) J. Chem. Soc., Perkin Trans. 2 , pp. 1713
- Garrido, J.M.P.J.¹ Delerue-Matos, C.² Borges, F.³ Macedo, T.R.A.⁴ Oliveira-Brett, A.M.⁵

17
- 0345529001
- McCamley, K.; Ripper, J. A.; Singer, R. D.; Scammells, P. J. J. Org. Chem. 2003, 68, 9847.
- (2003) J. Org. Chem , vol.68 , pp. 9847
- McCamley, K.¹ Ripper, J.A.² Singer, R.D.³ Scammells, P.J.⁴

18
- 0013796623
- (a) Pai, B. R.; Shanmugasundaram, G. Tetrahedron 1965, 21, 2579.
- (1965) Tetrahedron , vol.21 , pp. 2579
- Pai, B.R.¹ Shanmugasundaram, G.²

19
- 35348827257
- (b) Singh, O. V.; Huang, W.-J.; Chen, C.-H.; Lee, S.-S. Tetrahedron Lett. 2007, 48, 8166.
- (2007) Tetrahedron Lett , vol.48 , pp. 8166
- Singh, O.V.¹ Huang, W.-J.² Chen, C.-H.³ Lee, S.-S.⁴

20
- 4244056124
- Berényi, S.; Makleit, S.; Szilágyi, L. Acta Chim. Hung. 1984, 117, 307.
- (1984) Acta Chim. Hung , vol.117 , pp. 307
- Berényi, S.¹ Makleit, S.² Szilágyi, L.³

21
- 0032783037
- Yamaguchi, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. New J. Chem. 1999, 23, 799.
- (1999) New J. Chem , vol.23 , pp. 799
- Yamaguchi, K.¹ Mizugaki, T.² Ebitani, K.³ Kaneda, K.⁴

22
- 0035929108
- Choudary, B. M.; Bharathi, B.; Venkat Reddy, C.; Kantam, M. L.; Raghavan, K. V. Chem. Commun. 2001, 1736.
- (2001) Chem. Commun , pp. 1736
- Choudary, B.M.¹ Bharathi, B.² Venkat Reddy, C.³ Kantam, M.L.⁴ Raghavan, K.V.⁵

23
- 0022192604
- (a) Berényi, S.; Makleit, S.; Rantal, F. Acta Chim. Hung. 1985, 120, 201.
- (1985) Acta Chim. Hung , vol.120 , pp. 201
- Berényi, S.¹ Makleit, S.² Rantal, F.³

24
- 0039264708
- (b) Simon, C.; Berényi, S.; Makleit, S.; Fekete, V. Acta Chim. Hung. 1987, 124, 497.
- (1987) Acta Chim. Hung , vol.124 , pp. 497
- Simon, C.¹ Berényi, S.² Makleit, S.³ Fekete, V.⁴

25
- 0029745178
- (c) Hosztafi, S.; Makleit, S. Synth. Commun. 1996, 26, 3909.
- (1996) Synth. Commun , vol.26 , pp. 3909
- Hosztafi, S.¹ Makleit, S.²

26
- 34547870571
- (d) Sipos, A.; Debreceni, Sz.; Szabó, R.; Gyulai, Zs.; Berényi, S. Synth. Commun. 2007, 37, 2549.
- (2007) Synth. Commun , vol.37 , pp. 2549
- Sipos, A.¹ Debreceni, S.² Szabó, R.³ Gyulai, Z.⁴ Berényi, S.⁵

27
- 41649094980
- (e) Berényi, S.;Kiss, B.; Schmidt, É.; Greiner, I. Bioorg. Med. Chem. 2008, 16, 3773.
- (2008) Bioorg. Med. Chem , vol.16 , pp. 3773
- Berényi, S.¹ Kiss, B.² Schmidt, E.³ Greiner, I.⁴

28
- 48249156509
- General Procedure for the N-Substitution of Aporphines Apocodeine base (2.92 mmol) and Na2WO4 (300 mg, 1.02 mmol) was dissolved in H2O-l,4-dioxane (1:2, 10 mL) and cooled to 0 °C for the dropwise addition of H2O2 30% w/v, 12 mmol, The reaction mixture was stirred at r.t. for 3.5 h. The excess H2O 2 was quenched by addition of small portions of MnO2 at 0 °C and the presence of the peroxide determined by KI-starch paper. The reaction mixture, containing some overoxidized product as dark precipitation, was then vacuum filtered through a short pad of Celite. Solvent was removed in vacuo to give the crude product as a pale brown solid. It was immediately turned into hydrochloride salt by dissolving in a few drops of CHCl3 and dropping some EtOH sat. with HCl gas. After filtration, the mixture of minor apocodeine-HCl and major apocodeine N-oxide-HCl was dissolved in MeOH
- 3), 53.71 (C6a),43.56(C5), 37.18 (C7), 26.66 (C4). (-)-(R)-N-Propyl-2-bromonorapocodeine (44) and (-)-(R)-N-propyl-2-bromonorapomorphine (10) are characterized in ref. 16a.

29
- 0030002601
- Csutorás, Cs.; Berényi, S.; Makleit, S. Synth. Commun. 1996, 26, 2251.
- (1996) Synth. Commun , vol.26 , pp. 2251
- Csutorás, C.¹ Berényi, S.² Makleit, S.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.